


That's Not How I Imagined It Would Go

by Asgardian_prince



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Attempt at Humor, Castiel Loves Dean Winchester, Castiel and Dean Winchester First Meet, Coming Out, Cute, Dean Winchester & Sam Winchester Friendship, Dean Winchester Loves Castiel, Dean Winchester Talks About Feelings, Engaged Castiel/Dean Winchester, Established Castiel/Dean Winchester, Everyone Ships Castiel/Dean Winchester, Everything is Beautiful and Nothing Hurts, Family Dinners, Family Feels, Firefighter Dean Winchester, Fluff, Happy Dean Winchester, M/M, Mary Winchester Ships Castiel/Dean Winchester, Medic Castiel (Supernatural), Meet-Cute, Multi, Nice John Winchester, Sam Winchester Knows, Sam Winchester Ships Castiel/Dean Winchester, clueless John winchesters, marry winchester knows, mild description of a fire
Language: English
Status: Completed
Published: 2020-09-10
Updated: 2020-09-10
Packaged: 2021-03-06 22:13:38
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,291
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26396215
Author URL: https://archiveofourown.org/users/Asgardian_prince/pseuds/Asgardian_prince
Summary: Dean has been waiting for the perfect moment to tell his family about his big secret relationship.He plans to host the traditional family dinner in his house for the first time. And to do it right, he hid every evidence that he shares his home with someone else. Everything looked perfect, nothing could give away his secret, well exceptHe forgot to hide his engagement ring.
Relationships: Castiel/Dean Winchester, John Winchester/ Marry Winchester, Sam Winchester/Jessica Moore
Comments: 2
Kudos: 227





	That's Not How I Imagined It Would Go

Dean took one final look at his house.

It appeared that everything was neat and ready... No scratch that, he  knew  that everything was ready. he was  just paranoid.

  
Paranoid that this whole dinner will turn into a shit show because his brother will find a sock that didn't belong to him and find out his secret .  _Well..._ _the secret you plan to uncover tonight anyway, so why does it matter!_   
a very wise part of his mind contributed. But a wiser one added:  _no if you're going to do this you better do it right ... double double-check everything._

  
Which is how he ended up checking and double-checking under every surface looking for anything that might not belong to him . M ainly single socks. (knowing someone is  constantly losing those). He  was finished just  in time to open the door to greet his family.   


The Winchesters were a very close family.  And despite the long distance between  each and every one of them, they keep up with the tradition of family dinners at least once a month . And due to lousy excuses Dean kept coming up with ,(though some were legitimate mind you. ) this was Dean's first time hosting it in his new home. 2 years old new home, but you get the meaning. 

  
" Hey Honey. " his mom said hugging him and giving him a quick kiss to his cheek. followed by his dad holding a covered plate and a bottle of wine, each in a hand.

  
“ Where should I put these, son.” John said raising the bottle as a salute.

  
“I’ll take care of it. Y ou guys make yourselves comfortable in the living room.’’ he took what smelled a lot like his mom’s homemade apple pie and heads for the kitchen.  ‘’ Sam texted me, he’s like five minutes away, we’ll wait for him before starting for dinner, yeah ? ” he yelled back.

  
“ Sure honey, we can wait,” 

" Would you like a tour while we wait? " Dean suggests and both his parents agree. 

  
As the tour ended with Dean showing his parents to the guest room they'll be using in their stay there, Sam rang the doorbell signaling his arrival .    
" Everyone is here then. Who's ready to eat? " Dean asked.

  
" I will be once I use the bathroom," said Marry.

  
'' Sure, you can use the one attached to the guest room. " Dean pointed the direction to the stairs. Explaining the malfunction in the one downstairs. 

  
Once everything  was settled , the table was set and the food served. The Winchester family sat together on the dining table like a million times before. With nothing but smiles and cheerful laughs to  be shared . 'Cause this was the kind of loving happy family they've always been. So Dean's mind was at ease with the upcoming subject he planned to break to his family after dinner. Nope, he wasn't nervous at all. Except that he was, that is.

What he was afraid of, or rather nervous about wasn't his family's reaction to the news itself. But the secrecy Dean insisted upon for his entire life . He knew his parents and little brother were progressive open-minded people. And they loved him  dearly . That much was common knowledge. And they wanted to be as involved in their boys' lives as they could be.  So Dean  was scared he might hurt their feeling when they find out he was hiding a big chunk of himself in a closet for so damn long . But here goes nothing, he  just needed a good opener to the subject. 

  
Still stuck in his own thoughts, only half-listening to Sam's 'oh so exciting' case he'll be handling all on his own next month . His mom cleared her throat pulling him back to reality. 

  
" Something on your mind Dean ? " she said with a soft smile. 

  
_Is this the opener ?_ his mind demanded.  But no, he had a plan.  He'll wait till dessert time, while they  were gathered in the living room and bribed with his mom's homemade pie .

  
" No nothing . " he lied, buying himself more Time ''  just listening to you guys.'' 

  
'' Yeah? " Marry keeps smiling in suspicion," you look deep in thoughts. Is there something we should know about ? "  _where is this coming from mom?_

  
" What do you mean? '' he decides to play it cool for now.

  
" Well... I noticed earlier that I had a broken fingernail that kept on scratching me. So while I was in the bathroom; I looked for a nail clipper in your cabins. I swear baby I wasn't snooping around in your things, I  just happen to find it in your junk drawer. " Marry explained  casually while pulling  _it out of her pocket._

  
oh shit 

_oh shit_

  
Marry put the little square black box on the table for everyone to see.  He made sure that he hid everything, every single little thing. that might unravel someone else lives here too. But he forgot to hide THAT. 

  
_What a dumb fuck_

Dean didn't know what to do. What to say.

He felt the heat crawling up to his face, and he knew how red he must look right now. That's not how it  was supposed to go.  He had plans to start his monologue with a joke.  Maybe some shared memories and a few laughs, and then tell them about it. But now ... He felt cornered and out of control. like he was  being held at gunpoint and demanded to give information to save his life. 

  
" Dean? ... Dean are you okay ? " that was his dad's voice. The tone suggested that he's been calling his name for a while.

Dean looked up from the box to see all his family members looking at him in obvious concern. I t's okay, that doesn't change anything you can still do this.    
'' Uhm, yeah I'm good, dad .'' Dean cleared his throat. He reached to grab the box staring at everyone from the center of the table but John beat him to it, Opend it , and snatched the silver ring nuzzled inside. 

  
"I mean it's definitely beautiful. But it's too simple don't you think? "John said turning the ring between his thumb and forefinger. All the while Sam's shouting " let me see, let me see !" like a 4-year-old.

"  Obviously , you know your woman best, but let me tell you something she'll tell you she likes it to your face. But once she shows it to her friends they'll start complaining about the missing rock. '' Sam's examining the ring now. 

  
'' Oh " Sam  suddenly whispered more to himself than to anyone. He looked kind of shocked. And why isn't Dean stopping  all of this? why isn't he saying anything?    
'' John '' Marry warns.

" What it's true, if he wants her to say yes he needs the perfect ring . and everyone knows diamonds are the way to a woman's heart ''. 

  
Dean  was shocked , to say the least. Frozen in time mouth half-open , mind racing.  The voice of his parent arguing about whether Dean's girl would say yes to the ring or the man offering it, and whether Dean can afford a Diamond ring, were nothing but background noises .   
Dean was still staring at his engagement ring in Sam's hand. Who was placing it back to its box and looked like he was about to hand it back to Dean? Bless his soul that guy  really gets him. When  suddenly Sam shouts clapping his hands. 

  
'' Oh my god, guys shut up ''. On command, everyone looks at Sam. 

  
Dean took the ring his brother was offering. " Can you let him speak, please. " Sam said. 

  
_Do I want to? I should say something, yes. But what ? they think I'm proposing to some girl._

" Well, uh ... I-'' he started, cleared his throat, then start again ''-Well you see it's not  really what you guys think. '' 

  
_Okay, that's a good start. Now what?_

  
" So you're not  secretly dating someone and considering to pop a certain question ? '' he's mom asked again. 

'' Uh, well ... Yes and No ''

" Then what's the ring for? " 

  
" It, uh .. kinda for me? " Why was he asking his dad that! 

  
" I'm not following " 

  
"Okay, this is taking too long. J ust rip off the bandage won't ya"  _thanks, Sammy_ . 

  
"  Fine, okay, here's the thing: I'm not proposing to anyone. The ring is for me, as in someone proposed to me instead. ''

  
Dean felt the blush creeping up to his face again. All eyes were on him, and he was analyzing everyone's reaction  patiently . He's mom and Sam were smiling again. Good sign. But john's face was still neutral. _D_ _on't know what to make of that._

  
" Dear god son. You left her waiting so long, she had to do it herself.  Really ? Haven't I taught you anything about treating women.'' John finally said.

_Still D_ _on't know what to make of that._

  
" Dad why are you so stupid. "

Yes, they were that kind of a loving family. The kind where the little child calls his dad out when he's being an idiot.  And the father doesn't take offense to it because if everyone was giving him a Winchester Bitch-Face™ . Then he must've  really been an idiot.

  
Dean laughed at his dad's reaction to Sam's words, and felt encouraged by the current vibe around him. A pparently Sam and Marry were all caught up to the story and were happy for him anyway. Marry even gave him a little nod to enlighten his dad furthermore.

  
" Not a woman dad, I'm dating a guy, okay? And he proposed to me earlier this week. That's why there's no big rock on the ring. I don't like diamonds. '' 

  
" Oh .'' Was all john says for a while. The silence stretched for a while and Dean was starting to panic again.

  
"Oooh. " he says again. '' I  really didn't see that coming. " More silence. And then John starts to laugh, and everyone joined him.

Dean can't help but laugh too, though for different reasons. He  was relieved , he was happy that his family was fine with it. He knew he was nowhere near done with this conversation but he  was allowed to enjoy this small victory.

  
When the laughter died over. They agreed to finish their cooled down forgotten dinner before continuing with Dean's story. Which makes Dean grateful for Sam's existence once more. Because this gave him time to compose his thoughts and go back to his original plan.

  
They finished dinner accompanied by regular conversations of: work, daily routines, Sam's relationship with Jess, and other safe topics  .  No one mentioned Dean's love life until the table  was cleared , the dishes were clean and everyone  was settled with a plate of pie and ice cream back on the living room .

" C'mon , aren't you at least going to tell us if you said yes ? " Sam asked  impatiently . He looked very proud of himself for waiting this long to ask.

  
" Yes " Dean replied  simply .

  
" Yes as in ? " John always the slowest demanded. 

  
" Yes as in, I am getting married. " That managed to make his family bombard him with more questions.( and some squeels) all at once. He didn't get half of them.

  
"Then why aren't you wearing your ring ? "

  
" How come you never told us about him? " 

  
" Since when do you date men ? " 

  
" What's he's name ? " 

  
" Do we know him ? "

  
" When were you planning to tell us?"

  
" How long have you been together ? Are you sure about marrying him ? "

  
"Have you settled on a date yet ?"

  
"When are we meeting him ?'' 

  
" Okay, guys enough. " He raised his voice above everyone else's. Or tried to anyway. His mom was still squeeling in btween questions. " One question at a time, please. " 

  
They  just kept staring to each other. Unable de decide who should go first so Dean decided for them. He answered the few questions he got from that rambling. 

  
'' I'm not wearing my ring, because I wanted to tell you about him first and  hopefully meet him. I had this whole thing planned to tell you today actually, but you know..." he says with a shrug.

  
" Oh honey i'm so sorry. '' Marry hugged him  sympathetically .

'' It's okay mom it's not you're fault . I was going to tell you anyway, you  just started the conversation earlier than expected. Besides I'm the idiot who hid the ring in our shared bathroom. '' that earned him a laugh .

"To answer your question dad, I have been dating men since my last year in high school. And I've been with this particular man for 3 years now. last week-end was our anniversary and he proposed to me then. '' 

  
'' I  really don't see how you never saw that coming dad. He was so obvious. " Sam said interrupting his mothers 'awwws' and heart eyes. 

  
"Hey! I was completely subtle and discreet about my sexuality you giant asshole. " 

  
" Yeah ? Dean no straight man hangs posters of shirtless muscled men on their bedroom "

  
" They're WWE wrestlers that's  basically their uniform. '' 

  
" Okay fine what about Dr.sexy ?'' sam said making his mom laugh. When Dean failed to answer he continued " And Benny Lafittee from the grocery store ?" 

  
"what about benny, he was a good friend ? " 

  
" You used to insist going to that specific store that was 10 blocks away. Even though there was one right down the streets. And took your time picking things,  just to stare at him longer." Marry said making Dean turn red for the third time that evening .

  
" You knew too ? " 

  
" Honey , your first crush was Freddie from Scooby doo. '' She said caressing his even redder cheek. And Sam  just laughed again, their dad joining him this time.

  
" And besides, that kid next door what was his name ? "

  
" Castiel " John said . " loved that kid " 

  
" yeah , so did Dean " Sam says . 

  
" I  secretly wanted you two to get together. " Marry added

" You know now that you mention it, you're right Dean was always around that kid. I didn't think anything of it at the time but you two  were attached to the hip. You were so sad when they moved out ." John contemplated.

  
" Hey , so was I . He was my friend too I  just wasn't in love with him '' Sam added feeling left out.

  
" You guys  really liked Cas that much ? " Dean asked  hesitantly . 

  
" Yeah , that boy was so polite, and you were always happy around him, me and your dad always said he was your angel "

" That makes things so much easier " Dean says .

  
" Makes what easier? " Sam asked.

  
" You know I wasn't planning to make my engagement official until you guys met him and actually liked each other . Of course I never had any doubs about you liking him. But the fact that you're telling me you already love him makes things so easy."  just like that Dean reaches for his pocket , pulling his ring from its box and puts it on his finger. Fitting  perfectly in its place .

  
" No way " Sam says . 

  
" I'm sorry , what's going on now ?" John exclaimed . _S_ _eriously Dad keep up_ .

  
" Castiel's my fiancé " Dean said , not even trying to hide the massive grin on his face.

  
Dean's statement raised a round of cheerful excited noises all around him. But he couldn't get anything from it because he's mom was quealing on his left ear . 

  
" How did that heppen? " Sam asked .

  
'' We met on a job during a night shift. " Dean told them how ,  probably one of his worst jobs ever made him run into the love of his life since high school . 

  
He was a firefighter. Three years ago, a certain call had him running inside a massive building burning up. It was on the verge of collapsing, and a few people were still stuck inside. Dean and his team were responsible for evacuating the building. Although they managed to do so with the least damage possible ( considering ). He couldn't shake the horror of that night for a long time.  When Dean pulled the last child who was hiding underneath his bad. He had to give up his own oxygen mask from his face to give it to the little scared boy,because no one would've been able to reach them with a spare before the roof collapsed. So Dean, even though he held his breath as much as he could, still had lungs full of smoke by the time he got out to safety. 

It was just his luck that he had a very good, very hot medic to watch over him till his lungs were clean again. He recognized those baby blue eyes instantly .And it didn't take longer to fall back in love with them either.

  
" That was a heroic job you pulled there Dean. " These were the first words he heard when the dizziness of the adrenaline rush wore off... And that's how he knew his childhood crush remembered him too. Cas made an appointment the following night for drinks

'' Consider it an appreciation for your bravery." He had said with a wink. Dean wanted to take him on it right then but he still had 6 more hours to his shift , and apparently so did Cas.

  
So they met the following night. When they found out their 'fling' 15 years ago wasn't based on just teenage hormones, they set up a date the week after. It was difficult for them to find appropriate time to spend together . Their schedules was a huge obstacle . Dean seemed to work nights when Cas worked the day shift and vice versa . And the only reason Cas worked the night shift when they met was to cover up for a colleague on a sick leave. But as their relationship status developed, they organised their schedules so they could get sick of each others constant presence. ( as if ).  
Two and a half years ago, and six months into their relationship, they moved into this house together. Their friends gave them hell for it because they thought it was too soon$, but it wasn't for them. The distance was killing them , and it felt to Dean like they knew each other since forever. Like the 15 years gap in their past was nonexistent .

Cas was his best friend before he was his boyfriend, and it made what they shared even more profound. So he didn't care what his friends tought. As much as he loved them for caring and worrying about him they didn't feel what he felt for Cas, or what Cas felt for him. Which Dean was certain was the same. He could feel it in every touch and gaze from his love. And it made him the happiest Man alive.

  
" Honey I'm so happy for you. " Marry said hugging her son.

  
" When do we get to meet him then. " John said smiling . 

  
" Well he's at a boot camp for a month. He's till got another week before he comes back home. How about we set up another dinner then ? " 

  
" Sounds good to me . I really miss that guy. " Sam said.

  
" And then we'll plan the engagement party.'' marry said.

  
_Can't believe you were ever scared of this day._

When Dean imagined coming out to his family, he never expected to be disowned or anything like that. He was just scared he would be treated or looked at differently. But apparently that was never a problem with them, they knew all along. (Except for John of course ) and they loved him still. Better yet they loved Cas. Dean can't believe how free he feels right now . How that weight in his shoulder had lifted and let him finally breathe. From now on this would be his best memory ,topped only by the day he'd finally say 'I do' to a certain blue-eyed angel. And maybe far in the future hugging a blue eyed baby in his arms. 'Cause god only knows , h e was a sucker for blue eyes now 


End file.
